Acetonitrile → N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide

HRID 539789Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([CH:17]=3)[NH2:16])=[CH:10][N:4]2[N:3]=1.C(#N)C.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([NH:16][C:24](=[O:25])[C:23]([CH3:28])([CH3:27])[CH3:22])[CH:17]=3)=[CH:10][N:4]2[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 40 mL vial is charged with 5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-aniline (0.85 g, 3.28 mmol), acetonitrile (14 mL) and pyridine (0.450 mL). The mixture is added trimethylacetyl chloride (0.628 mL, 0.0051 mol) and stirred for 20 min at 80° C. The mixture is concentrated, taken up in EtOAc (35 mL) and washed once with HCl (20 mL, 1M) and then NaOH (20 mL, 1M). Organic layer is dried, concentrated and purified on silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (1.05 g, 94% yield). LCMS m/z=343.5 [M+H]+, tR=2.39 min. (compound same as Example 118)

Workup

concentrationThe mixture is concentrated
washwashed once with HCl (20 mL, 1M)
customOrganic layer is dried
concentrationconcentrated
custompurified on silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-6f5f20083bd443a9ab54ab51fbdd8f81
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

Loading…